How should a trilby fit?

Good day folks,

So I recently stumbled upon an article on trilbies and fedoras on Fashionbeans. I have always been in love with hats and since I feel like I could pull them off (just wanted to wear them out once in a while), I was about to go downtown and look for one (in wool, black, maybe with a satin band). I have tried a few sizes, but since there is no real professional hat shop where I live, I was wondering: How should a trilby fit? Especially, when does it sit to low and when to high? I tried one that I thought was really nice, though it slightly touches my ears when I had it on (there is no smaller size in stock anymore), is that ok or is this a big "no-no"? Should it sit on my head comfortably without touching them or am I being to paranoid? Of course, it shouldn't push them away from my head, I guess, so is it ok to slightly tuck them into the hat?

I think all these guys pull off the Trilby well and they're all rockin' it differently. While it's not my particular thing (I love my hair too much!), the right shape and colour can compliment an outfit well regardless of how you let it sit on your head

Hats can be tricky, and you probably won't get too much love for the trilby on here. I think it can work though.

Not sure where you're from, but about 15 years ago in the UK, there was a bit of a trend for wearing dodgy pinstripe versions on a night out, with distressed bootcut jeans and pointy tan shoes. Maybe an open waistcoast thrown in for good measure. Basically looking like a '90s Robbie Savage. Not a good look.

Also, as men wear hats less than decades ago, the rules and etiquette have been forgotten. I'm not saying that these have to be adhered to absolutely strictly, but I was in a nice restaurant recently, and a guy across the room was wearing a flat cap at the table. I wanted to hurt him.

I think the key to making it look good, as with all things style-related, is not looking self-conscious in it. Rock it with manly confidence. I don't wear hats very often either (I too love my hair too much, and I don't think they actually suit me that well), but when I do, I try and keep it classic and uncomplicated - the hat is enough of a statement - trilby with a bit of tailoring, flat cap with a more rugged work-wear look.

In terms of the fit, just try to avoid looking like you're wearing your dad's hat. If you're tucking your ears in, then it's probably too big I would've thought. Mine just about grazes the top of my ears. I think that's about right. I'm no expert though. Should be plenty of advice online.

In terms of how to wear it - that's personal preference. If you listen to Sinatra (and when it comes to wearing hats, I think we all should), then the angle you wear it at conveys your mood - tipped slightly back for an open, approachable look; pulled lower over the eyes for that brooding thing. Unless you're an R&B singer, maybe don't tilt it too much to the side... But then again, experiment, see what suits, see what you're comfortable with, what you're trying to convey. I tend to wear mine tipped back slightly. Not full-on Olly Murs territory, but just enough so that I don't look like a 1950s spy.

Hats are not easy to pull off in this day and age, as they are a statement piece. But go for it I say. I wish more men wore hats (proper hats I mean - not snapbacks etc), and I wish I had the balls to wear one every day! Good luck.

How should a trilby fit? Especially, when does it sit to low and when to high? I tried one that I thought was really nice, though it slightly touches my ears when I had it on (there is no smaller size in stock anymore), is that ok or is this a big "no-no"? Should it sit on my head comfortably without touching them or am I being to paranoid? Of course, it shouldn't push them away from my head, I guess, so is it ok to slightly tuck them into the hat?

Generally, a hat should sit comfortably on your head, coming to a point on the sides of your head a little above the ears. The fact is that hats are rarely tailored to you and so long as they look ok on you probably don't have to worry. One that sits on your ears (or where you can tuck your ears inside) is too big, however - walk away and find a better fitting one. If the hat is just slightly too large you might be able to put a small band of cloth or similar within the inner hat band to help it stay on better.